Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H27N5O2 |
| Molecular Weight | 441.5249 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CC2=C(O1)C=CC(=C2)N3CCN(CCCCC4=CNC5=C4C=C(C=C5)C#N)CC3
InChI
InChIKey=SGEGOXDYSFKCPT-UHFFFAOYSA-N
InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)
| Molecular Formula | C26H27N5O2 |
| Molecular Weight | 441.5249 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9098681
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9098681
Vilazodone is a serotonergic antidepressant. The mechanism of the antidepressant effect of vilazodone is not fully understood but is thought to be related to its inhancement of serotonergic activity in the CNS through selective inhibition of serotonin reuptake. Vilazodone is also a partial agonist at serotonergic 5-HT1A receptors; however, the net result of this action on serotonergic transmission and its role in vilazodone’s antidepressant effect are unknown. The side effects include activation of mania/hypomania in patients with bipolar disorder, seizures can occur with treatment in patients with a seizure disorder.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12183683 |
0.5 nM [IC50] | ||
Target ID: CHEMBL214 |
0.2 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | VIIBRYD Approved UseIndicated for the treatment of major depressive disorder (MDD) Launch Date2011 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
156 ng/mL |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VILAZODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1645 ng × h/mL |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VILAZODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
25 h |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VILAZODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VILAZODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Overview
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 58, (ClinPharm) 19, 22-23, 37-40, 90 |
moderate [IC50 2.8 uM] | |||
Page: 58, (ClinPharm) 19, 23, 37-39, 41-42, 90 |
moderate [Ki 7.37 uM] | |||
Page: 58, (ClinPharm) 23, 47-49 |
no | |||
Page: 58, (ClinPharm) 23 |
no | |||
Page: 58, (ClinPharm) 23, 47-49 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18 Page: (ClinPharm) 18 |
no | |||
Page: 58, (ClinPharm) 18, 23, 47-49 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58 Page: 58.0 |
no | |||
Page: 58, (ClinPharm) 23, 47-49 |
no | |||
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
no | no (co-administration study) Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with caffeine (100 mg QD on Day 10) to healthy subjects resulted in a small (9%) decrease in paraxanthine/caffeine plasma ratio (8-h post dose). Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
||
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
no | no (co-administration study) Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with flurbiprofen (50 mg QD on Day 10) to healthy subjects resulted no effect in CYP2C9 activity (4'-hydroxyflurbiprofen urinal recovery (0-8 hr)/flurbiprofen AUC0-8 (L/h)). Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
||
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
no | weak (co-administration study) Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with mephenytoin (100 mg QD on Day 10) to healthy subjects resulted in a small (11%) increase in mephenytoin biotransformation. Page: 58, (ClinPharm) 18, 23, 47-49, 89-94 |
||
Page: (ClinPharm) 16, 19, 42-45, 45-47, 90 |
unlikely [IC50 >6.3 uM] | |||
Page: 58, (ClinPharm) 22, 37-40, 42-45 |
weak [IC50 68 uM] | |||
Page: 58, (ClinPharm) 22-23, 41-42, 90 |
weak [Ki 24 uM] | |||
Page: 58, (ClinPharm) 22-23, 41-42, 90 |
weak [Ki 81.7 uM] | |||
Page: (ClinPharm) 18, 47-49, 89-94 |
weak | no (co-administration study) Comment: 2.4-fold mRNA expression (60 hr incubation with human hepatocytes from two donors); Coadministration of vilazodone (20 mg QD for 10 days) with debrisoquine (10 mg QD on Day 10) to healthy subjects resulted in a small (10%) increase in 4'-hydroxydebrisoquine/debrisoquine total urinary recovery ratio (0-8 hr post dose). Page: (ClinPharm) 18, 47-49, 89-94 |
||
Page: (ClinPharm) 18, 47-49, 89-94 |
weak | no (co-administration study) Comment: 2.2-fold mRNA expression (60 hr incubation with human hepatocytes from two donors); Coadministration of vilazodone (20 mg QD for 10 days) with nifedipine (20 mg QD on Day 8) to healthy subjects resulted in no change in Nifedipine AUC0-inf and a small increase (13%) in Cmax. Page: (ClinPharm) 18, 47-49, 89-94 |
||
Page: (Label) 12 |
weak | yes (co-administration study) Comment: Coadministration of Vilazodone slightly increased Digoxin (P-gp substrate) AUC and Cmax (less than 25%). Page: (Label) 12 |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58 Page: 58.0 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39 |
likely | |||
Page: 58, (ClinPharm) 14, 18, 21, 22, 23, 37-39, 82-84 |
major | yes (co-administration study) Comment: Ketoconazole (200 mg QD for 13 days), a strong CYP3A4 inhibitor, increased vilazodone (5 mg or 10 mg QD on Day 4) systemic exposure (AUC0-t) by 42% (5 mg), 51% (10 mg), and Cmax by 48% (5 mg), 38% (10 mg), Human liver microsomes (specific inhibitor: troleandomycin 50 mcM) Page: 58, (ClinPharm) 14, 18, 21, 22, 23, 37-39, 82-84 |
||
Page: 58, (ClinPharm) 18, 22, 37-39 |
minor | |||
Page: 58, (ClinPharm) 18, 22, 37-39 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39 |
unlikely |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=48 Page: 48.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Issues encountered in recent attempts to develop novel antidepressant agents. | 2015-05 |
|
| Psychotropic exposures in pediatric patients: Symptomatic iloperidone and vilazodone ingestions. | 2015-03 |
|
| Identification of hydrolytic and isomeric N-oxide degradants of vilazodone by on line LC-ESI-MS/MS and APCI-MS. | 2015-01 |
|
| Relative efficacy and tolerability of vortioxetine versus selected antidepressants by indirect comparisons of similar clinical studies. | 2014-12 |
|
| A review of the clinical efficacy, safety and tolerability of the antidepressants vilazodone, levomilnacipran and vortioxetine. | 2014-12 |
|
| Bioavailability comparison of a new form of vilazodone XVII to IV in beagles using liquid chromatography/mass spectrometry. | 2014-12 |
|
| Efficacy and safety of vilazodone in major depressive disorder: a randomized, double-blind, placebo-controlled trial. | 2014-11 |
|
| Efficacy of vilazodone on anxiety symptoms in patients with major depressive disorder. | 2014-11 |
|
| A validated LC-MS/MS method for the rapid quantification of vilazodone in rat plasma: application to a pharmacokinetic study. | 2014-09 |
Sample Use Guides
Recommended target dosage: 20 mg to 40 mg once daily with food. To titrate: start with initial dosage of 10 mg once daily for 7 days, followed by 20 mg once daily. The dose may be increased up to 40 mg once daily after a minimum of 7 days between dosage increases. Prior to initiating VIIBRYD, screen for bipolar disorder.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
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on
Edited
Mon Mar 31 18:08:48 GMT 2025
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| Record UNII |
S239O2OOV3
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C265
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WHO-ATC |
N06AX24
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LIVERTOX |
NBK548223
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QN06AX24
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S239O2OOV3
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CHEMBL439849
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m11446
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C494040
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DB06684
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S239O2OOV3
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Vilazodone
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C90716
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4223
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> INHIBITOR |
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET->PARTIAL AGONIST | |||
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EXCRETED UNCHANGED |
FECAL; URINE
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> INHIBITOR |
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Volume of Distribution | PHARMACOKINETIC |
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IV infusion |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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